Adding fuel to the iTunes11 make-over fire, new rumors are making the rounds that suggest Apple's do-over will include much better iCloud integration. Which, of course, makes the kind of sense that does. Bloomberg teases:

Apple will unveil the changes by year’s end, said the people, who asked not to be identified because the plans aren’t public. The company will more closely integrate its iCloud file- storage service with iTunes so users can more seamlessly access and manage their music, videos and downloaded software apps across different Apple gadgets, the people said. Apple also plans new features for sharing music, the people said.

Sources all tell Bloomberg that Apple is working to improve file management, given the huge amount of content now available in the various iTunes, iBook, and App Stores.

That includes changes to how users find new material and how they access what they already own on different Apple devices

Part of this is said to include sharing, and they claim Apple is trying to negotiate more photos and pictures to accompany music, as well as the rights for a user to listen to a song sent to them by another user. (Would that require a return of DRM for single-use song promos?) The existing Twitter integrated, and new fangled Facebook integration would be included as well.

On the oft-rumored Apple subscription music service, Bloomberg's sources disagree. Apple's oft-stated belief is that people prefer to own their music, but as competition increases and generations change, it's inevitable they'd investigate all options.

What remains to be seen is whether or not Apple takes any new iTunes version as an opportunity to de-bloat the aging, saggy app. On iOS they've pulled music and video and iBooks apart, separated iTunes Store, App Store, and iBook, and now added distinct iTunes U and Podcasts apps.

Since Apple still maintains cross-compatibility with Windows in iTunes, it's no doubt easier for them to simply port one big app, but at some point doing everything becomes doing nothing, at least not well.

If they follow Google and allow limited plays, DRM shouldn't be a major issue. Just allow a person to play then remove it. I'd welcome that, if I were an iTunes user.
The big difference there is it is easier to do this on the web than in desktop software but iCloud could prove helpful here.

Re: "Since Apple still maintains cross-compatibility with Windows in iTunes..."
I wonder exactly how important that cross-compatibility really is. If Apple ever wants to use Siri as a front-end for iTunes searches on OS X (more on that later), then that cross-compatibility gets broken. (Extremely unlikely Apple would ever port Siri to anything Microsoft.)
So yes, having one big cross-compilable project is convenient for Apple. But that convenience can't be worth holding back iTunes' evolution on OS X. Let Windows users have their big old monolithic app. They're used to inconvenience and frustration after all.
Oh, and maybe Siri won't officially be out of beta until it's running on Macs as well as iOS devices.

Are they going to do anything about how Siri sounds like Madeeya (or Tyler Perry in a dress)? Cuz that's the thing that bugs me more than anything else about Siri. At least Google sounds like a woman. Come on Apple.